9 Songs I Have in My iTunes You (Probably) Don’t Know But Should

A few months ago I wrote about the 5 songs I was ashamed were taking up room in my iTunes collection. The appropriate follow-up? A celebration of my music, particularly the semi-obscure. Thus, my journey through my iTunes began. I pulled some of my favorites of the not-entirely-so-mainstream artists that’s music is part of my regular iTunes experience and worthy of your valuable listening time, as well.

My sister introduced me to Beth Orton. I admit I haven’t listened to much of her music, but you can’t argue with this song. The Five Stairsteps originally released it in the 1970s, and while an excellent version, Orton’s take on the song appeals to my sad-song obsession. It’s slower, more soothing, and, overall, pure beauty.

Okay, I know the lead singer’s grandparents. But I genuinely love these songs and this band, which hails from Charleston. And if you ever have the chance to see them live, do it. They’re real deal. I promise.

Like Beth Orton, Dar Williams entered my musical playlist because of my sister. I admit I don’t like all of Williams’s music, but these two in particular are in my frequently listened category. Williams follows a more storytelling route in her music, and both of these songs showcase that style. “February” is heartbreaking, although its actual meaning is still a mystery. Listen to it and tell me what you think. My sister and I share a theory, one we think is obvious, yet many exist. “The Babysitter’s Here” is one of my sister’s favorites and over the past few months has become one of mine, too. It’s a lovely look at life in the sixties through a child’s perspective.

I got this song through a free download on iTunes but I instantly fell in love. The line, “She’s a dancer, when she dances she is free” grabbed me the first time. Her voice in mellow and folksy, backed by an acoustic guitar. It’s the perfect song to listen to on a mellow drive through the country.

Mmmmm, Joshua Radin. Aside from being completely adorable, Joshua Radin’s voice is so smooth and pleasant that I want to eat it up like a bowl of ice cream. He’s friends with Zach Braff and did a collaboration with Ingrid Michaelson (one of my other personal favorites). Their song “Sky” is equally worth a listen, but the song “Brand New Day” is probably my all time favorite of his. It’s so sing-songy and upbeat. It makes me think of summer, dusk, and fireflies.

I listened to this song on repeat for at least a week. Her deep voice is irresistable and the song has an old school feel, reminding me of songwriting legends the likes of Carole King (which, if you don’t own Tapestry, do yourself a favor and buy it NOW). The rest of the Happenstance album is a mainstay in my collection, but this song makes me happy while others are better for a day of longing.

Oh, Stephen Kellogg. It was a fateful evening at DePauw that brought me to SK6RS for the first time. Their poorly attended free concert in the gym turned me into a convert, alongside 40 of my fellow students. Since then I’ve seen the band twice, loving them a little more each time. Not only are they great musicians, but they’re funny, lively, and personable, making the concert going experience feel like they just crashed your home and are giving a private show for you and your friends in your living room. This song is my favorite and is on their album The Glassjaw Boxer. But don’t just stop here. Please check out the rest of their music.